Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/30—Low-molecular-weight compounds
  • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
  • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
  • C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/08—Processes
  • C08G18/16—Catalysts
  • C08G18/22—Catalysts containing metal compounds
  • C08G18/24—Catalysts containing metal compounds of tin
  • C08G18/242—Catalysts containing metal compounds of tin organometallic compounds containing tin-carbon bonds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/30—Low-molecular-weight compounds
  • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
  • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
  • C08G18/3863—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms
  • C08G18/3865—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms containing groups having one sulfur atom between two carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
  • C08G18/722—Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
  • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
  • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
  • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
  • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
  • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
  • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
  • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
  • C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
  • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
  • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
  • G02B1/041—Lenses
• • G—PHYSICS
  • G02—OPTICS
  • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
  • G02C7/00—Optical parts
  • G02C7/02—Lenses; Lens systems ; Methods of designing lenses

Definitions

• the present disclosure relates to a polymerizable composition containing a polyisocyanate compound and a polythiol compound, an optical component obtained from the polymerizable composition, a plastic lens containing the optical component, and a spectacle lens including a lens substrate including the optical component.
• Patent Literature 1 a plastic lens with high refractive index can be obtained by reacting a polyisocyanate compound with a polythiol compound (see, Patent Literature 1, for example).
• Patent Literature 1 a sulfur-containing urethane-based resin lens which is obtained by heating and curing a composition containing tetrathiol and at least one ester compound selected from a polyisocyanate compound, a polyisothiocyanate compound, and an isothiocyanate compound having an isocyanate group is disclosed. It is described that the lens is colorless and transparent and has a physical property of excellent heat resistance due to high refractive index and low dispersion and also excellent productivity.
• Patent Literature 1 JP 7-252207 A
• Patent Literature 1 is problematic in that, as a cross-linked structure is formed at low temperature in order to use tetrathiol, viscosity increase is fast during the polymerization and striae are easily generated compared to other urethane resin-based plastic lenses.
• an object of one example of the present disclosure is to provide a polymerizable composition allowing obtainment of an optical component with reduced striae, an optical component obtained from the polymerizable composition, a plastic lens containing the optical component, and a spectacle lens including a lens substrate including the optical component.
• an object of one example of the present disclosure is to provide a polymerizable composition allowing obtainment of an optical component with excellent tensile strength, an optical component obtained from the polymerizable composition, a plastic lens containing the optical component, and a spectacle lens including a lens substrate including the optical component.
• the inventors of the present disclosure conducted intensive studies. As a result, it was found that, by using a polymerizable composition which contains an isocyanate component containing pre-determined alicyclic polyisocyanate and pre-determined non-cyclic aliphatic polyisocyanate and a polythiol component containing pre-determined polythiol, the above problems can be solved, and the present disclosure is completed accordingly. Namely, the present disclosure is as described below.
• a polymerizable composition including; an isocyanate component which contains alicyclic polyisocyanate (A-1) having two or more isocyanate groups and non-cyclic aliphatic polyisocyanate (A-2) having two or more isocyanate groups; and a polythiol component which contains polythiol (B-1) having four or more mercapto groups and two or more sulfide bonds and polythiol (B-2) having two or three mercapto groups and two or three ester bonds.
• a spectacle lens including a lens substrate which includes the optical component according to [2].
• a polymerizable composition allowing obtainment of an optical component with reduced striae, an optical component obtained from the polymerizable composition, a plastic lens containing the optical component, and a spectacle lens including a lens substrate including the optical component can be provided.
• a polymerizable composition allowing obtainment of an optical component with excellent tensile strength, an optical component obtained from the polymerizable composition, a plastic lens containing the optical component, and a spectacle lens including a lens substrate including the optical component can be provided.
• the polymerizable composition of the present disclosure contains an isocyanate component which contains alicyclic polyisocyanate (A-1) having two or more isocyanate groups and non-cyclic aliphatic polyisocyanate (A-2) having two or more isocyanate groups, and a polythiol component which contains polythiol (B-1) having four or more mercapto groups and two or more sulfide bonds and polythiol (B-2) having two or three mercapto groups and two or three ester bonds.
• the isocyanate component used for the polymerizable composition of the present disclosure contains the alicyclic polyisocyanate (A-1) having two or more isocyanate groups and the non-cyclic aliphatic polyisocyanate (A-2) having two or more isocyanate groups.
• the alicyclic polyisocyanate (A-1) may have two isocyanate groups.
• Examples of the alicyclic polyisocyanate (A-1) include isophorone diisocyanate, methylene biscyclohexyl diisocyanate, bis(isocyanatemethyl)cyclohexane, bis(isocyanatemethyl)bicyclo[2.2.1]heptane, methylcyclohexane diisocyanate, dicyclohexylmethane diisocyanate, dimethyldicyclohexylmethane diisocyanate, and dicyclohexyldimethylmethane diisocyanate. These alicyclic polyisocyanates may be used either singly or in combinations or two or more types.
• the alicyclic polyisocyanate (A-1) may be at least one selected from a group consisting of isophorone diisocyanate, methylene biscyclohexyl diisocyanate, bis(isocyanatemethyl)cyclohexane, and bis(isocyanatemethyl)bicyclo[2.2.1]heptane.
• an optical component which is produced by using the polymerizable composition it may be at least one selected from a group consisting of isophorone diisocyanate, 4,4′-methylene biscyclohexyl diisocyanate, 1,3-bis(isocyanatemethyl)cyclohexane, and bis(isocyanatemethyl)bicyclo[2.2.1]heptane.
• the non-cyclic aliphatic polyisocyanate (A-2) may have two isocyanate groups.
• non-cyclic aliphatic polyisocyanate examples include hexamethylene diisocyanate, butene diisocyanate, butadiene diisocyanate, bis(isocyanateethyl)carbonate, and bis(isocyanateethyl) ether. These polyisocyanates may be used either singly or in combinations or two or more types.
• the non-cyclic aliphatic polyisocyanate (A-2) may be at least one selected from a group consisting of hexamethylene diisocyanate and trimethylhexamethylene diisocyanate.
• the isocyanate component of the polymerizable composition of the present disclosure may contain, within a range in which the effect of the present disclosure is not impaired, polyisocyanate other than the alicyclic polyisocyanate (A-1) and the non-cyclic aliphatic polyisocyanate (A-2), if necessary.
• the ratio of the total of the alicyclic polyisocyanate (A-1) and the non-cyclic aliphatic polyisocyanate (A-2) in the isocyanate component used for the polymerizable composition of the present disclosure may be, relative to the total mass of the isocyanate component, 80% by mass or more, 90% by mass or more, 95% by mass or more, and 100% by mass or less.
• the ratio of the total of the alicyclic polyisocyanate (A-1) and the non-cyclic aliphatic polyisocyanate (A-2) is 80% by mass or more, the effect of suppressing striae of an optical component to be obtained can be further enhanced. Furthermore, it is also possible to improve the tensile strength of an optical component which is produced by using the polymerizable composition of the present disclosure.
• the molar ratio [(A-1)/(A-2)] between the alicyclic polyisocyanate (A-1) and the non-cyclic aliphatic polyisocyanate (A-2) may be, from the viewpoint of further improving the effect of suppressing striae of an optical component to be obtained, 95/5 to 50/50, 90/10 to 50/50, and 90/10 to 60/40.
• the molar ratio is within the above range, the tensile strength of an optical component which is produced by using the polymerizable composition of the present disclosure can be improved.
• the polythiol component used in the polymerizable composition of the present disclosure contains the polythiol (B-1) having four or more mercapto groups and two or more sulfide bonds and the polythiol (B-2) having two or three mercapto groups and two or three ester bonds.
• the polythiol (B-1) may have four mercapto groups.
• polythiol (B-1) may have three or more sulfide bonds and may have three sulfide bonds.
• polythiol (B-1) examples include bis(mercaptomethyl)trithiaundecanedithiol, mercaptomethylbismercaptodithiaoctane, bis(mercaptomethyl)dithiane, bis(mercaptomethylthio)dithiane, and (bis(mercaptomethylthio)ethyl)dithietane.
• the polythiols (B-1) may be used either singly or in combinations or two or more types.
• the polythiol (B-1) may be bis(mercaptomethyl)trithiaundecanedithiol, at least one selected from a group consisting of 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, and: a mixture of 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecanedithiol, at least one selected from a group consisting of 4,8-bis(mercap
• polythiol (B-2) examples include trimethylol propane tris(thioglycolate), trimethylol propane tris(mercaptopropionate), butanediol bis(thioglycolate), butanediol bis(mercaptopropionate), diethylene glycol bis(mercaptoacetate), diethylene glycol bis(mercaptopropionate), ethylene glycol bis(mercaptoacetate), ethylene glycol bis(mercaptopropionate), and pentaerythritol tetrakis (2-mercaptoacetate). These polythiols may be used either singly or in combinations or two or more types.
• the polythiol (B-2) may be at least one selected from a group consisting of trimethylol propane tris(thioglycolate), trimethylol propane tris(mercaptopropionate), butanediol bis(thioglycolate), and butanediol bis(mercaptopropionate), and at least one selected from a group consisting of trimethylol propane tris(thioglycolate), trimethylol propane tris(3-mercaptopropionate), 1,4-butanediol bis(thioglycolate), and 1,4-butanediol bis(3-mercaptopropionate).
• the polythiol (B-2) having three mercapto groups may be at least one selected from a group consisting of trimethylol propane tris(thioglycolate) and trimethylol propane tris(mercaptopropionate), and may be at least one selected from a group consisting of trimethylol propane tris(thioglycolate) and trimethylol propane tris(3-mercaptopropionate).
• the polythiol component of the polymerizable composition of the present disclosure may contain, within a range in which the effect of the present disclosure is not impaired, polythiol other than the polythiol (B-1) and the polythiol (B-2), if necessary.
• the polymerizable composition which may be among the polymerizable compositions of the present disclosure may be as follows:
• the alicyclic polyisocyanate (A-1) is at least one selected from a group consisting of isophorone diisocyanate, methylene biscyclohexyl diisocyanate, bis(isocyanatemethyl)cyclohexane, and bis(isocyanatemethyl)bicyclo[2.2.1]heptane,
• non-cyclic aliphatic polyisocyanate (A-2) is at least one selected from a group consisting of hexamethylene diisocyanate and trimethylhexamethylene diisocyanate,
• the polythiol (B-1) is at least one selected from a group consisting of 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, and,
• the polythiol (B-2) is at least one selected from a group consisting of trimethylol propane tris(thioglycolate), trimethylol propane tris(3-mercaptopropionate), 1,4-butanediol bis(thioglycolate), and 1,4-butanediol bis(3-mercaptopropionate).
• the ratio of the total of the polythiol (B-1) and the polythiol (B-2) in the polythiol component used for the polymerizable composition of the present disclosure may be, relative to the total mass of the polythiol component, 70% by mass or more, 80% by mass or more, 90% by mass or more, and 100% by mass or less.
• the ratio of the total of the polythiol (B-1) and the polythiol (B-2) is 70% by mass or more, the effect of suppressing striae of an optical component to be obtained can be further enhanced. Furthermore, it is also possible to improve the tensile strength of an optical component which is produced by using the polymerizable composition of the present disclosure.
• the molar ratio [(B-1)/(B-2)] between the polythiol (B-1) and the polythiol (B-2) may be, from the viewpoint of further enhancing the effect of suppressing the striae of an optical component to be obtained, 90/10 to 50/50, 90/10 to 60/40, and 85/15 to 65/35.
• the molar ratio [(B-1)/(B-2)] is within the above range, the tensile strength of an optical component which is produced by using the polymerizable composition can be improved.
• the use ratio between the polythiol component and the polyisocyanate component may be, in terms of the functional group molar ratio between SH group and/NCO group, within a range of from 0.3 to 2.0, within a range of from 0.7 to 1.5, within a range of from 0.7 to 1.2, and within a range of from 0.8 to 1.1.
• the polymerizable composition of the present disclosure consists of the above isocyanate component and the above polythiol component only.
• the content of the total of the isocyanate component and the polythiol component may be 80% by mass or more, 90% by mass or more, 95% by mass or more, and 98% by mass or more and 100% by mass or less in the polymerizable composition.
• the polymerizable composition of the present disclosure may contain, within a range in which the effect of the present disclosure is not impaired, a component which is different from the components of the above isocyanate component and the above polythiol component.
• a component which is different from the components of the above isocyanate component and the above polythiol component examples include a compound which is copolymerizable with the above isocyanate component and the above polythiol component, an active hydrogen compound represented by amine, an epoxy compound, an olefin compound, a carbonate compound, an ester compound, a metal, a metal oxide, an organometallic compound, and an inorganic material. They may be used either singly or in combination of two or more types.
• reaction catalyst used for production of polythiourethane may be suitably added to the polymerizable composition of the present disclosure.
• the reaction catalyst include organic tin like dimethyl tin dichloride.
• the blending amount of the reaction catalyst may be, relative to the total amount of 100 parts by mass of the isocyanate component and polythiol component, 0.01 to 1 part by mass, 0.05 to 0.5 part by mass, and 0.08 to 0.3 part by mass.
• a releasing agent may be also added.
• the releasing agent include a phosphoric acid-based releasing agent such as butoxy ethyl acid phosphate or dibutoxy ethyl acid phosphate.
• the blending amount of the releasing agent may be, relative to the total amount of 100 parts by mass of the isocyanate component and polythiol component, 0.01 to 1 part by mass, 0.1 to 0.5 part by mass, and 0.2 to 0.3 part by mass.
• various materials including a chain extending agent, a cross-linking agent, a photostabilizer, a UV absorbing agent, an anti-oxidizing agent, an oil-soluble dye, a filler, a releasing agent, and a blueing agent may be added to the polymerizable composition of the present disclosure.
• the optical component of the present disclosure is obtained by polymerizing the polymerizable composition of the present disclosure.
• the optical component of the present disclosure may be produced as described below, for example.
• the method for producing an optical component includes a step of carrying out cast polymerization of the polymerizable composition.
• the polymerizable composition of the present disclosure is degassed, if necessary, and injected thereafter to a molding die. Then, the polymerizable composition injected to a molding die is polymerized.
• a molding die consisting of a pair of glass mold or metal mold and a tape- or resin-based gasket is used.
• the polymerization time for polymerizing the polymerizable resin in a molding die is 3 to 96 hours, for example.
• the polymerization temperature is 0 to 130 degrees, for example.
• the optical component of the present disclosure is suitably used as an optical component of an optical device such as a spectacle lens or a camera lens.
• the plastic lens of the present disclosure includes the optical component of the present disclosure, and may be a spectacle lens including a lens substrate including the optical component of the present disclosure.
• the plastic lens of the present disclosure exhibits the effect of having reduced striae, high index, low dispersion, and low specific gravity. Furthermore, the plastic lens of the present disclosure has excellent tensile strength.
• the plastic lens of the disclosure may consist of the optical component of the present disclosure only, or it may contain other optical component.
• an anti-reflection treatment or a surface polishing and dyeing treatment for having a fashion property or the like can be carried out for the optical component of the present disclosure.
• the spectacle lens may have at least one selected from a group consisting of an anti-static layer, a hard coating layer, an anti-reflection layer, and a light illuminating layer on top of the lens substrate consisting of the optical component of the present disclosure.
• n e represents the refractive index when measurement is made with a wavelength of e ray
• n F′ represents the refractive index when measurement is made with a wavelength of F′ ray
• n C′ represents the refractive index when measurement is made with a wavelength of C′ ray.
• the obtained plastic lens was observed with a naked eye according to Schlieren method, and striae of the plastic lens was evaluated based on the following three levels.
• the plastic lens with evaluation result of VG or G has practically no problem in terms of striae.
• the plastic lens with the evaluation result of B is not suitable for practical use.
• the obtained plastic lens was observed with a naked eye under a fluorescent lamp in dark room, and transparency of the plastic lens was evaluated based on the following three levels.
• the plastic lens with evaluation result of VG or G has practically no problem in terms of transparency.
• the plastic lens with the evaluation result of B is not suitable for practical use.
• the obtained plastic lens was observed with a naked eye using a strain scope, and optical distortion of the plastic lens was evaluated based on the following three levels.
• the plastic lens with evaluation result of VG or G has practically no problem in terms of optical distortion.
• the plastic lens with the evaluation result of B is not suitable for practical use.
• plastic lenses of the following Examples, Comparative Examples, and Reference Examples were produced as described below.
• IPDI isophorone diisocyanate
• HDI hexamethylene diisocyanate
• TMTG trimethylol propane tris(thioglycolate)
• Product name: JP-506H was degassed under reduced pressure of 5 mmHg to prepare a homogeneously-prepared monomer mixture.
• the resulting monomer mixture was injected to a molding die which consists of a pair of glass molds and a gasket made of resin. Furthermore, as for the pair of glass molds, a pair with top mold curvature of 600 mm and bottom mold curvature of 120 mm was used, and thus the molding die was assembled such that the center thickness of a plastic lens becomes 5 mm and the diameter of a plastic lens becomes 75 mm.
• the temperature was raised from 20 degrees to 120 degrees over 15 hours followed by heat polymerization for 4 hours at 120 degrees. After cooling, by extracting the plastic lens from the molding die, the plastic lens of Example 1 was obtained.
• the plastic lens of Example 2 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 43.6 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 34.2 parts by mass, the blending amount of HDI was modified to 8.2 parts by mass, and the blending amount of TMTG was modified to 14.0 parts by mass.
• the plastic lens of Example 3 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 34.2 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 42.4 parts by mass, the blending amount of HDI was modified to 17.3 parts by mass, and the blending amount of TMTG was modified to 6.1 parts by mass.
• the plastic lens of Example 4 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 42.7 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 26.4 parts by mass, the blending amount of HDI was modified to 8.1 parts by mass, and the blending amount of TMTG was modified to 22.8 parts by mass.
• the plastic lens of Example 5 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 35.8 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 36.4 parts by mass, the blending amount of HDI was modified to 14.6 parts by mass, and 13.2 parts by mass of trimethylol propane tris(3-mercaptopropionate) (hereinbelow, described as “TMTP”) was used instead of TMTG.
• TMTP trimethylol propane tris(3-mercaptopropionate
• the plastic lens of Example 6 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 40.5 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 37.5 parts by mass, the blending amount of HDI was modified to 11.3 parts by mass, and 10.7 parts by mass of 1,4-butanediol bis(mercaptoacetate) (hereinbelow, described as “BDTG”) was used instead of TMTG.
• BDTG 1,4-butanediol bis(mercaptoacetate
• the plastic lens of Example 7 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 33.3 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 36.6 parts by mass, the blending amount of HDI was modified to 16.8 parts by mass, and 13.3 parts by mass of 1,4-butanediol bis(mercaptopropionate) (hereinbelow, described as “BDTP”) was used instead of TMTG.
• BDTP 1,4-butanediol bis(mercaptopropionate
• the plastic lens of Example 8 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 38.2 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 40.5 parts by mass, the blending amount of TMTG was modified to 5.8 parts by mass, and 15.5 parts by mass of trimethylhexamethylene diisocyanate (hereinbelow, described as “TMDI”) was used instead of HDI.
• TMDI trimethylhexamethylene diisocyanate
• the plastic lens of Example 9 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 32.6 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 40.3 parts by mass, 20.6 parts by mass of TMDI was used instead of HDI, and 6.5 parts by mass of TMTP was used instead of TMTG.
• the plastic lens of Example 10 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 37.7 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 35.5 parts by mass, 15.3 parts by mass of TMDI was used instead of HDI, and 11.5 parts by mass of BDTG was used instead of TMTG.
• the plastic lens of Example 11 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 42.4 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 34.9 parts by mass, 10.0 parts by mass of TMDI was used instead of HDI, and 12.7 parts by mass of BDTP was used instead of TMTG.
• the plastic lens of Example 12 was produced by preparing a polymerizable composition in the same manner as Example 1 except that 37.3 parts by mass of dicyclohexylmethane diisocyanate (hereinbelow, described as “HMDI”) was used instead of IPDI, the blending amount of the polythiol (B-1-1) was modified to 32.6 parts by mass, the blending amount of HDI was modified to 16.0 parts by mass, and the blending amount of TMTG was modified to 14.1 parts by mass.
• HMDI dicyclohexylmethane diisocyanate
• the plastic lens of Example 13 was produced by preparing a polymerizable composition in the same manner as Example 12 except that the blending amount of HMDI was modified to 47.8 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 35.5 parts by mass, the blending amount of HDI was modified to 7.7 parts by mass, and 9.1 parts by mass of TMTP was used instead of TMTG.
• the plastic lens of Example 14 was produced by preparing a polymerizable composition in the same manner as Example 12 except that the blending amount of HMDI was modified to 37.8 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 39.6 parts by mass, the blending amount of HDI was modified to 16.2 parts by mass, and 6.4 parts by mass of BDTP was used instead of TMTG.
• the plastic lens of Example 15 was produced by preparing a polymerizable composition in the same manner as Example 12 except that the blending amount of HMDI was modified to 36.3 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 38.1 parts by mass, 19.4 parts by mass of TMDI was used instead of HDI, and 6.1 parts by mass of TMTP was used instead of TMTG.
• the plastic lens of Example 16 was produced by preparing a polymerizable composition in the same manner as Example 12 except that the blending amount of HMDI was modified to 42.2 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 37.9 parts by mass, 14.5 parts by mass of TMDI was used instead of HDI, and 5.5 parts by mass of BDTG was used instead of TMTG.
• the plastic lens of Example 17 was produced by preparing a polymerizable composition in the same manner as Example 1 except that 42.9 parts by mass of bis(isocyanatemethyl)cyclohexane (hereinbelow, described as “HXDI”) was used instead of IPDI, the blending amount of the polythiol (B-1-1) was modified to 27.0 parts by mass, the blending amount of HDI was modified to 4.1 parts by mass, and 26.1 parts by mass of TMTP was used instead of TMTG.
• HXDI bis(isocyanatemethyl)cyclohexane
• the plastic lens of Example 18 was produced by preparing a polymerizable composition in the same manner as Example 17 except that the blending amount of HXDI was modified to 42.9 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 38.1 parts by mass, the blending amount of HDI was modified to 6.6 parts by mass, and 12.4 parts by mass of BDTG was used instead of TMTP.
• the plastic lens of Example 19 was produced by preparing a polymerizable composition in the same manner as Example 17 except that the blending amount of HXDI was modified to 29.1 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 32.1 parts by mass, 21.0 parts by mass of TMDI was used instead of HDI, and 17.8 parts by mass of TMTG was used instead of TMTP.
• the plastic lens of Example 20 was produced by preparing a polymerizable composition in the same manner as Example 17 except that the blending amount of HXDI was modified to 34.8 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 39.9 parts by mass, 16.1 parts by mass of TMDI was used instead of HDI, and 9.2 parts by mass of BDTG was used instead of TMTP.
• the plastic lens of Example 21 was produced by preparing a polymerizable composition in the same manner as Example 1 except that 52.0 parts by mass of bis(isocyanatemethyl)bicyclo[2.2.1]heptane (hereinbelow, described as “NBDI”) was used instead of IPDI, the blending amount of the polythiol (B-1-1) was modified to 28.5 parts by mass, the blending amount of HDI was modified to 3.7 parts by mass, and the blending amount of TMTG was modified to 15.8 parts by mass.
• NBDI bis(isocyanatemethyl)bicyclo[2.2.1]heptane
• the plastic lens of Example 22 was produced by preparing a polymerizable composition in the same manner as Example 21 except that the blending amount of NBDI was modified to 52.3 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 30.7 parts by mass, the blending amount of HDI was modified to 3.8 parts by mass, and 13.3 parts by mass of BDTG was used instead of TMTG.
• the plastic lens of Example 23 was produced by preparing a polymerizable composition in the same manner as Example 21 except that the blending amount of NBDI was modified to 34.8 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 28.6 parts by mass, 18.8 parts by mass of TMDI was used instead of HDI, and 17.8 parts by mass of TMTP was used instead of TMTG.
• the plastic lens of Example 24 was produced by preparing a polymerizable composition in the same manner as Example 21 except that the blending amount of NBDI was modified to 35.8 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 35.7 parts by mass, 19.3 parts by mass of TMDI was used instead of HDI, and 9.2 parts by mass of BDTP was used instead of TMTG.
• the plastic lens of Comparative Example 1 was produced by preparing a polymerizable composition in the same manner as Example 12 except that the blending amount of HMDI was modified to 58.9 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 41.1 parts by mass, and HDI and TMTG were not used.
• the plastic lens of Comparative Example 2 was produced by preparing a polymerizable composition in the same manner as Example 12 except that the blending amount of HMDI was modified to 46.6 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 43.4 parts by mass, and the blending amount of HDI was modified to 10.0 parts by mass, and TMTG was not used.
• the plastic lens of Comparative Example 3 was produced by preparing a polymerizable composition in the same manner as Example 12 except that the blending amount of HMDI was modified to 58.1 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 36.9 parts by mass, 4.9 parts by mass of pentaerythritol tetrakis(mercaptopropionate) (hereinbelow, described as “PTMP”) was used instead of TMTG, and HDI was not used.
• PTMP pentaerythritol tetrakis(mercaptopropionate
• the plastic lens of Comparative Example 4 was produced by preparing a polymerizable composition in the same manner as Example 17 except that the blending amount of HXDI was modified to 51.4 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 48.6 parts by mass, and HDI and TMTG were not used.
• the plastic lens of Comparative Example 5 was produced by preparing a polymerizable composition in the same manner as Example 17 except that the blending amount of HXDI was modified to 36.8 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 49.6 parts by mass, the blending amount of HDI was modified to 13.6 parts by mass, and TMTP was not used.
• the plastic lens of Comparative Example 6 was produced by preparing a polymerizable composition in the same manner as Example 21 except that the blending amount of NBDI was modified to 58.7 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 41.3 parts by mass, and HDI and TMTG were not used.
• the plastic lens of Comparative Example 7 was produced by preparing a polymerizable composition in the same manner as Example 21 except that the blending amount of NBDI was modified to 36.9 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 43.3 parts by mass, 19.9 parts by mass of TMDI was used instead of HDI, and TMTG was not used.
• the plastic lens of Comparative Example 8 was produced by preparing a polymerizable composition in the same manner as Example 1 except that 50.7 parts by mass of xylylene diisocyanate (hereinbelow, described as “XDI”) was used instead of IPDI, the blending amount of the polythiol (B-1-1) was modified to 49.3 parts by mass, and HDI and TMTG were not used.
• XDI xylylene diisocyanate
• the plastic lens of Comparative Example 9 was produced by preparing a polymerizable composition in the same manner as Comparative Example 8 except that the blending amount of XDI was modified to 52.7 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 44.3 parts by mass, and 2.6 parts by mass of thioglycerin (hereinbelow, described as “TG”) was used.
• the plastic lens of Comparative Example 10 was produced by preparing a polymerizable composition in the same manner as Comparative Example 8 except that the blending amount of XDI was modified to 49.9 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 38.9 parts by mass, and 11.3 parts by mass of dimercaptomethyldithiane (hereinbelow, described as “DMMD”) was used.
• DMMD dimercaptomethyldithiane
• the plastic lens of Reference Example 1 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 54.8 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 45.2 parts by mass, and HDI and TMTG were not used.
• the plastic lens of Reference Example 2 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 29.4 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 48.4 parts by mass, the blending amount of HDI was modified to 22.2 parts by mass, and TMTG was not used.
• the plastic lens of Reference Example 3 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 33.3 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 45.7 parts by mass, 21.0 parts by mass of TMDI was used instead of HDI, and TMTG was not used.
• the plastic lens of Reference Example 4 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 54.1 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 40.1 parts by mass, the blending amount of TMTG was modified to 5.8 parts by mass, and HDI was not used.
• the plastic lens of Reference Example 5 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 53.7 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 39.9 parts by mass, 6.4 parts by mass of TMTP was used instead of TMTG, and HDI was not used.
• the plastic lens of Reference Example 6 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 54.1 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 40.1 parts by mass, 5.8 parts by mass of BDTG was used instead of TMTG, and HDI was not used.
• the plastic lens of Reference Example 7 was produced by preparing a polymerizable composition in the same manner as Example 1 except that the blending amount of IPDI was modified to 53.7 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 39.9 parts by mass, 6.4 parts by mass of BDTP was used instead of TMTG, and HDI was not used.
• the plastic lens of Reference Example 8 was produced by preparing a polymerizable composition in the same manner as Example 12 except that the blending amount of HMDI was modified to 53.1 parts by mass, the blending amount of the polythiol (B-1-1) was modified to 41.3 parts by mass, 5.6 parts by mass of hexylisocyanate (hereinbelow, described as “HI”) was used instead of HDI, and TMTG was not used.
• the plastic lenses of Examples 1 to 24 were satisfactory in terms of the item for evaluating the striae. They are also satisfactory in terms of the item for evaluating the refractive index, Abbe number, transparency, and optical distortion. On the other hand, the plastic lenses of Comparative Examples 1 to 10 were not satisfactory in terms of the item for evaluating the striae. Based on this, it was possible to confirm that, by using a polymerizable composition containing an isocyanate component which contains the alicyclic polyisocyanate (A-1) and the non-cyclic aliphatic polyisocyanate (A-2) and a polythiol component which contains the polythiol (B-1) and the polythiol (B-2), a plastic lens with reduced striae can be obtained.
• the plastic lenses of Reference Examples 1 to 7 were satisfactory in terms of the item for evaluating the striae.
• the evaluation item relating to tensile strength was significantly poorer compared to the plastic lenses of Examples 1 to 24. Based on this, it was possible to confirm that, when the alicyclic polyisocyanate (A-1) and the polythiol (B-1) are used and also any one of the non-cyclic aliphatic polyisocyanate (A-2) and the polythiol (B-2) is used, a plastic lens with reduced striae can be produced but the tensile strength of the lens becomes very low.
• the plastic lens of Reference Example 8 was satisfactory in terms of the item for evaluating the striae.
• the evaluation item relating to tensile strength was significantly poorer compared to the plastic lenses of Examples 1 to 24. Based on this, it was possible to confirm that, when a polymerizable composition containing the alicyclic polyisocyanate (A-1), the polythiol (B-1), and hexyl isocyanate (HI) is used, a plastic lens with reduced striae can be produced but the tensile strength of the lens becomes very low.
• One embodiment of the present disclosure is a polymerizable composition containing an isocyanate component which contains the alicyclicpolyisocyanate (A-1) having two or more isocyanate groups and the non-cyclic aliphatic polyisocyanate (A-2) having two or more isocyanate groups, and a polythiol component which contains the polythiol (B-1) having four or more mercapto groups and two or more sulfide bonds and the polythiol (B-2) having two or three mercapto groups and two or three ester bonds.
• an isocyanate component which contains the alicyclicpolyisocyanate (A-1) having two or more isocyanate groups and the non-cyclic aliphatic polyisocyanate (A-2) having two or more isocyanate groups
• a polythiol component which contains the polythiol (B-1) having four or more mercapto groups and two or more sulfide bonds and the polythiol (B-2) having
• a polymerizable composition allowing obtainment of an optical component with reduced striae, an optical component obtained from the polymerizable composition, a plastic lens containing the optical component, and a spectacle lens including a lens substrate including the optical component can be provided.

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